AU2001274459C1 - Pharmaceutical compositions comprising cannabidiol derivatives - Google Patents
Pharmaceutical compositions comprising cannabidiol derivatives Download PDFInfo
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- AU2001274459C1 AU2001274459C1 AU2001274459A AU2001274459A AU2001274459C1 AU 2001274459 C1 AU2001274459 C1 AU 2001274459C1 AU 2001274459 A AU2001274459 A AU 2001274459A AU 2001274459 A AU2001274459 A AU 2001274459A AU 2001274459 C1 AU2001274459 C1 AU 2001274459C1
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
- QHMBSVQNZZTUGM-ZWKOTPCHSA-N cannabidiol Chemical class OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-ZWKOTPCHSA-N 0.000 title abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 35
- 230000008569 process Effects 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 238000011282 treatment Methods 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 7
- 241000282414 Homo sapiens Species 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 61
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 230000036407 pain Effects 0.000 claims description 8
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- -1 dimethoxy compound Chemical class 0.000 claims description 6
- 150000002118 epoxides Chemical class 0.000 claims description 6
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 claims description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 2
- DYDCAPNFPHATGL-UHFFFAOYSA-N [Mg+]C.CC(C)[N-]C1CCCCC1 Chemical compound [Mg+]C.CC(C)[N-]C1CCCCC1 DYDCAPNFPHATGL-UHFFFAOYSA-N 0.000 claims description 2
- 230000021736 acetylation Effects 0.000 claims description 2
- 238000006640 acetylation reaction Methods 0.000 claims description 2
- 238000007075 allylic rearrangement reaction Methods 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000007884 disintegrant Substances 0.000 claims description 2
- 238000006735 epoxidation reaction Methods 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 235000013355 food flavoring agent Nutrition 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 238000011160 research Methods 0.000 claims description 2
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 claims description 2
- 229960002218 sodium chlorite Drugs 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 208000028017 Psychotic disease Diseases 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 230000002920 convulsive effect Effects 0.000 claims 3
- 230000004968 inflammatory condition Effects 0.000 claims 3
- 230000000926 neurological effect Effects 0.000 claims 3
- 239000006184 cosolvent Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000002563 ionic surfactant Substances 0.000 claims 1
- 239000000787 lecithin Substances 0.000 claims 1
- 229940067606 lecithin Drugs 0.000 claims 1
- 235000010445 lecithin Nutrition 0.000 claims 1
- 239000002736 nonionic surfactant Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 150000003626 triacylglycerols Chemical class 0.000 claims 1
- 230000000202 analgesic effect Effects 0.000 abstract description 7
- 230000000049 anti-anxiety effect Effects 0.000 abstract description 7
- 230000002082 anti-convulsion Effects 0.000 abstract description 7
- 239000002249 anxiolytic agent Substances 0.000 abstract description 7
- 230000001093 anti-cancer Effects 0.000 abstract description 5
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 4
- 230000000561 anti-psychotic effect Effects 0.000 abstract description 4
- 230000000324 neuroprotective effect Effects 0.000 abstract description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 3
- 150000001336 alkenes Chemical class 0.000 description 76
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 76
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 35
- 229950011318 cannabidiol Drugs 0.000 description 30
- QHMBSVQNZZTUGM-UHFFFAOYSA-N Trans-Cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 QHMBSVQNZZTUGM-UHFFFAOYSA-N 0.000 description 29
- ZTGXAWYVTLUPDT-UHFFFAOYSA-N cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CC=C(C)C1 ZTGXAWYVTLUPDT-UHFFFAOYSA-N 0.000 description 29
- 238000005160 1H NMR spectroscopy Methods 0.000 description 28
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 27
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 20
- 230000000694 effects Effects 0.000 description 15
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 239000000284 extract Substances 0.000 description 11
- ZELUXPWDPVXUEI-ZWKOTPCHSA-N 7-hydroxycannabidiol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(CO)=C1 ZELUXPWDPVXUEI-ZWKOTPCHSA-N 0.000 description 10
- 239000002158 endotoxin Substances 0.000 description 10
- 229960000905 indomethacin Drugs 0.000 description 10
- 229920006008 lipopolysaccharide Polymers 0.000 description 10
- 108700012920 TNF Proteins 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 8
- 230000003110 anti-inflammatory effect Effects 0.000 description 7
- 229940114079 arachidonic acid Drugs 0.000 description 7
- 235000021342 arachidonic acid Nutrition 0.000 description 7
- 229930003827 cannabinoid Natural products 0.000 description 7
- 239000003557 cannabinoid Substances 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 229920000392 Zymosan Polymers 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 210000002540 macrophage Anatomy 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 230000003389 potentiating effect Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 206010014025 Ear swelling Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000006907 apoptotic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- PCXRACLQFPRCBB-ZWKOTPCHSA-N dihydrocannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)C)CCC(C)=C1 PCXRACLQFPRCBB-ZWKOTPCHSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 229940089151 indomethacin 20 mg Drugs 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VQPVHIFSDPRZAC-ZBUVYOTDSA-N (2r,3r)-2-(2,6-dimethoxy-4-pentylphenyl)-6-methylidene-3-prop-1-en-2-ylcyclohexan-1-ol Chemical compound COC1=CC(CCCCC)=CC(OC)=C1[C@H]1[C@H](C(C)=C)CCC(=C)C1O VQPVHIFSDPRZAC-ZBUVYOTDSA-N 0.000 description 2
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 2
- KZHNYLAFFGASBN-UHFFFAOYSA-N 1-methylidene-2-prop-1-en-2-ylcyclohexane Chemical compound CC(=C)C1CCCCC1=C KZHNYLAFFGASBN-UHFFFAOYSA-N 0.000 description 2
- YVEPGCZIBQXPJW-FZWXSHBKSA-N 2-[(1r,6r)-2-hydroxy-3-methylidene-6-prop-1-en-2-ylcyclohexyl]-5-pentylbenzene-1,3-diol Chemical compound OC1=CC(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(=C)C1O YVEPGCZIBQXPJW-FZWXSHBKSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- 0 C*c1c(C2C=C(C*)CCC2C(C)=C)c(OC)cc(*)c1 Chemical compound C*c1c(C2C=C(C*)CCC2C(C)=C)c(OC)cc(*)c1 0.000 description 2
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- 240000001307 Myosotis scorpioides Species 0.000 description 2
- 208000005141 Otitis Diseases 0.000 description 2
- 241000452413 Sabra Species 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 2
- 229940065144 cannabinoids Drugs 0.000 description 2
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 229960004242 dronabinol Drugs 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000000506 psychotropic effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinyl group Chemical group C1(O)=CC(O)=CC=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
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- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 1
- KEEKMOIRJUWKNK-CABZTGNLSA-N (2S)-2-[[2-[(4R)-4-(difluoromethyl)-2-oxo-1,3-thiazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide Chemical compound FC([C@H]1N(C(SC1)=O)C=1N=C2N(CCOC3=C2C=CC(=C3)N[C@H](C(=O)N)C)C=1)F KEEKMOIRJUWKNK-CABZTGNLSA-N 0.000 description 1
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- MPJURNPNPDQYSY-UHFFFAOYSA-N 5-(2-methyloctan-2-yl)-2-(3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl)benzene-1,3-diol Chemical compound OC1=CC(C(C)(C)CCCCCC)=CC(O)=C1C1C(C(C)=C)CCC(C)=C1 MPJURNPNPDQYSY-UHFFFAOYSA-N 0.000 description 1
- ZELUXPWDPVXUEI-UHFFFAOYSA-N 7-Hydroxy-cannabidiol Natural products OC1=CC(CCCCC)=CC(O)=C1C1C(C(C)=C)CCC(CO)=C1 ZELUXPWDPVXUEI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
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- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/065—Diphenyl-substituted acyclic alcohols
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0038—Radiosensitizing, i.e. administration of pharmaceutical agents that enhance the effect of radiotherapy
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/54—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
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- Public Health (AREA)
- Medicinal Chemistry (AREA)
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- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| IL136839 | 2000-06-16 | ||
| IL136839A IL136839A (en) | 2000-06-16 | 2000-06-16 | Pharmaceutical compositions comprising cannabidiol derivatives, and processes for the preparation of same |
| PCT/IL2001/000537 WO2001095899A2 (fr) | 2000-06-16 | 2001-06-12 | Compositions pharmaceutiques renfermant des derives de cannabidiol |
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| AU2001274459A1 AU2001274459A1 (en) | 2002-03-14 |
| AU2001274459B2 AU2001274459B2 (en) | 2005-07-07 |
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| AU7445901A Pending AU7445901A (en) | 2000-06-16 | 2001-06-12 | Pharmaceutical compositions comprising cannabidiol derivatives |
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| Application Number | Title | Priority Date | Filing Date |
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| AU7445901A Pending AU7445901A (en) | 2000-06-16 | 2001-06-12 | Pharmaceutical compositions comprising cannabidiol derivatives |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7759526B2 (fr) |
| EP (1) | EP1289517B1 (fr) |
| JP (1) | JP2004503498A (fr) |
| AT (1) | ATE309798T1 (fr) |
| AU (2) | AU2001274459C1 (fr) |
| CA (1) | CA2411831C (fr) |
| DE (1) | DE60115029T2 (fr) |
| DK (1) | DK1289517T3 (fr) |
| ES (1) | ES2254432T3 (fr) |
| IL (1) | IL136839A (fr) |
| WO (1) | WO2001095899A2 (fr) |
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| US6995187B1 (en) * | 1999-10-18 | 2006-02-07 | University Of Connecticut | Peripheral cannabinoid receptor (CB2) selective ligands |
| IL136839A (en) | 2000-06-16 | 2006-12-10 | Yissum Res Dev Co | Pharmaceutical compositions comprising cannabidiol derivatives, and processes for the preparation of same |
| US8449908B2 (en) * | 2000-12-22 | 2013-05-28 | Alltranz, Llc | Transdermal delivery of cannabidiol |
| WO2003063847A1 (fr) * | 2002-02-01 | 2003-08-07 | Gw Pharma Limited | Compositions comprenant du cannabinoides destinees au traitement de nausees, de vomissements, de mal des transports ou d'etats pathologiques similaires |
| GB0202385D0 (en) * | 2002-02-01 | 2002-03-20 | Gw Pharma Ltd | Compositions for the treatment of nausea,vomiting,emesis,motion sicknes or like conditions |
| IL148244A0 (en) | 2002-02-19 | 2002-09-12 | Yissum Res Dev Co | Anti-nausea and anti-vomiting activity of cannabidiol compounds |
| US7285687B2 (en) | 2002-04-25 | 2007-10-23 | Virginia Commonwealth University | Cannabinoids |
| IL157849A0 (en) * | 2003-09-10 | 2004-03-28 | Yissum Res Dev Co | Pharmaceutical compositions containing (+) cannabidiol and derivatives thereof and some such novel derivatives |
| IL159892A0 (en) * | 2004-01-15 | 2004-06-20 | Yissum Res Dev Co | Use of quinonoid derivatives of cannabinoids in the treatment of malignancies |
| EP1869063A2 (fr) * | 2005-03-29 | 2007-12-26 | Regents Of The University Of Minnesota | Procedes de production d'esters 3 bioactif d'aldehyde betulinique et d'acide betulinique |
| KR20080063800A (ko) | 2005-09-29 | 2008-07-07 | 에이엠알 테크놀로지, 인크. | 델타-9-테트라히드로칸나비놀의 제조 방법 |
| US20100158973A1 (en) | 2006-03-13 | 2010-06-24 | Hadasit Medical Research Services & Development Llimited | Therapeutic uses of cannabidiol compounds |
| US9763894B2 (en) | 2006-12-05 | 2017-09-19 | Virginia Commonwealth University | Inflammation therapy |
| WO2009018389A1 (fr) * | 2007-07-30 | 2009-02-05 | Alltranz Inc. | Promédicaments de cannabidiol, compositions comprenant les promédicaments de cannabidiol et leurs procédés d'utilisation |
| GB2456183A (en) * | 2008-01-04 | 2009-07-08 | Gw Pharma Ltd | Anti-psychotic composition comprising cannabinoids and anti-psychotic medicament |
| US20090247619A1 (en) * | 2008-03-06 | 2009-10-01 | University Of Kentucky | Cannabinoid-Containing Compositions and Methods for Their Use |
| WO2014062965A1 (fr) | 2012-10-17 | 2014-04-24 | Northeastern University | Ligands cannabinergiques de 2-cycloalkyl résorcinol |
| US9889100B2 (en) | 2013-05-02 | 2018-02-13 | Mor Research Applications Ltd. | Cannabidiol for treatment of severe and refractory graft-versus-host disease |
| EP2991733B1 (fr) | 2013-05-02 | 2020-02-19 | Mor Research Applications Ltd. | Cannabidiol destiné à la prévention et au traitement de la maladie du greffon contre l'hôte |
| GB2516814B (en) | 2013-06-19 | 2016-08-31 | Otsuka Pharma Co Ltd | Use of phytocannabinoids for increasing radiosensitivity in the treatment of cancer |
| GB2530001B (en) | 2014-06-17 | 2019-01-16 | Gw Pharma Ltd | Use of cannabidiol in the reduction of convulsive seizure frequency in treatment-resistant epilepsy |
| GB2527599A (en) * | 2014-06-27 | 2015-12-30 | Gw Pharma Ltd | Use of 7-OH-Cannabidiol (7-OH-CBD) and/or 7-OH-Cannabidivarin (7-OH-CBDV) in the treatment of epilepsy |
| GB2531282A (en) | 2014-10-14 | 2016-04-20 | Gw Pharma Ltd | Use of cannabinoids in the treatment of epilepsy |
| EP3232808B1 (fr) | 2014-12-19 | 2020-04-01 | THC Pharm GmbH The Health Concept | Boisson contenant du cbd |
| GB2539472A (en) | 2015-06-17 | 2016-12-21 | Gw Res Ltd | Use of cannabinoids in the treatment of epilepsy |
| MX2018000844A (es) | 2015-07-22 | 2018-07-06 | Phytopharma Int Ltd | Composiciones ingeribles por abejas, procedimientos para el uso de las mismas para producir miel y miel producida de esta manera. |
| US9585867B2 (en) | 2015-08-06 | 2017-03-07 | Charles Everett Ankner | Cannabinod formulation for the sedation of a human or animal |
| WO2017160923A1 (fr) * | 2016-03-15 | 2017-09-21 | Royal Oil Colorado Llc | Formulations d'huile d'argan et de cannabidiol |
| CA3077624A1 (fr) | 2016-10-01 | 2018-04-05 | James Smeeding | Compositions pharmaceutiques comprenant une statine et un cannabinoide et leurs utilisations |
| AU2018287018B2 (en) | 2017-06-20 | 2022-04-28 | University Of Guelph | Cannabidiolic acid esters compositions and uses thereof |
| IL272709B2 (en) | 2017-09-08 | 2024-09-01 | Scicann Therapeutics Inc | The compounds containing cannabinoid and spilantol |
| GB201806953D0 (en) | 2018-04-27 | 2018-06-13 | Gw Res Ltd | Cannabidiol Preparations |
| WO2019222459A1 (fr) * | 2018-05-18 | 2019-11-21 | Diverse Biotech, Inc. | Préparations de cannabinoïdes et utilisations thérapeutiques |
| JP2021535201A (ja) * | 2018-08-20 | 2021-12-16 | ベッソール ファルマ、エルエルシー | カンナビノイドの作成のためのプロセス |
| CN112062697B (zh) * | 2019-05-22 | 2023-09-01 | 上海特化医药科技有限公司 | 间苯多酚衍生物及其制备方法 |
| GB201910389D0 (en) * | 2019-07-19 | 2019-09-04 | Gw Pharma Ltd | Novel compounds, methods for their manufacture, and uses thereof |
| US20220401381A1 (en) | 2019-11-08 | 2022-12-22 | Vella Bioscience, Inc. | Peripherally acting cannabidiol (cbd)-containing compounds and uses thereof for enhancing female sexual function or treating female sexual disorders |
| CN111848365A (zh) * | 2020-07-16 | 2020-10-30 | 云南自由贸易试验区睿之成医药科技有限公司 | 一种大麻二酚的合成方法 |
| US12029718B2 (en) | 2021-11-09 | 2024-07-09 | Cct Sciences, Llc | Process for production of essentially pure delta-9-tetrahydrocannabinol |
| JP2023553335A (ja) | 2020-11-24 | 2023-12-21 | イッサム・リサーチ・ディベロップメント・カンパニー・オブ・ザ・ヘブルー・ユニバーシティ・オブ・エルサレム・リミテッド | カンナビノイド誘導体、及び、炎症、疼痛又は肥満の治療におけるそれらの使用 |
| WO2022133544A1 (fr) * | 2020-12-23 | 2022-06-30 | Botanix Pharmaceuticals Limited | Cannabinoïdes cbd et analogues de cannabinoïdes cbd |
| CN112898190B (zh) * | 2021-02-07 | 2023-10-24 | 中国科学院长春应用化学研究所 | 一种大麻二酚衍生物及其制备方法 |
| WO2022238700A1 (fr) | 2021-05-12 | 2022-11-17 | GW Research Limited | Dérivés de cannabidiol-c4 pour le traitement de l'épilepsie |
| WO2024069589A1 (fr) * | 2022-09-29 | 2024-04-04 | Blackstone Therapeutics, Llc | Analogues de cannabinoïdes et procédés d'utilisation pour le traitement et la prévention du cancer |
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| CH472435A (de) | 1965-06-02 | 1969-05-15 | Bayer Ag | Verfahren zur Herstellung von Estern phosphorhaltiger Säuren |
| US5538993A (en) * | 1991-09-12 | 1996-07-23 | Yissum Research Development Company | Certain tetrahydrocannabinol-7-oic acid derivatives |
| US5434295A (en) * | 1994-02-07 | 1995-07-18 | Yissum Research Development Company | Neuroprotective pharmaceutical compositions of 4-phenylpinene derivatives and certain novel 4-phenylpinene compounds |
| US5891465A (en) | 1996-05-14 | 1999-04-06 | Biozone Laboratories, Inc. | Delivery of biologically active material in a liposomal formulation for administration into the mouth |
| US6235741B1 (en) | 1997-05-30 | 2001-05-22 | Merck & Co., Inc. | Angiogenesis inhibitors |
| BR0009200A (pt) | 1999-03-22 | 2001-12-26 | Immugen Pharmaceuticals Inc | Compostos e composições para o tratamento dedoenças associada com disfunção imune |
| IL136839A (en) | 2000-06-16 | 2006-12-10 | Yissum Res Dev Co | Pharmaceutical compositions comprising cannabidiol derivatives, and processes for the preparation of same |
-
2000
- 2000-06-16 IL IL136839A patent/IL136839A/en not_active IP Right Cessation
-
2001
- 2001-06-12 CA CA2411831A patent/CA2411831C/fr not_active Expired - Fee Related
- 2001-06-12 DK DK01940973T patent/DK1289517T3/da active
- 2001-06-12 US US10/311,554 patent/US7759526B2/en not_active Expired - Fee Related
- 2001-06-12 ES ES01940973T patent/ES2254432T3/es not_active Expired - Lifetime
- 2001-06-12 WO PCT/IL2001/000537 patent/WO2001095899A2/fr active IP Right Grant
- 2001-06-12 AT AT01940973T patent/ATE309798T1/de not_active IP Right Cessation
- 2001-06-12 JP JP2002510078A patent/JP2004503498A/ja not_active Withdrawn
- 2001-06-12 DE DE60115029T patent/DE60115029T2/de not_active Expired - Lifetime
- 2001-06-12 EP EP01940973A patent/EP1289517B1/fr not_active Expired - Lifetime
- 2001-06-12 AU AU2001274459A patent/AU2001274459C1/en not_active Ceased
- 2001-06-12 AU AU7445901A patent/AU7445901A/xx active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US7759526B2 (en) | 2010-07-20 |
| IL136839A (en) | 2006-12-10 |
| DK1289517T3 (da) | 2006-04-03 |
| ATE309798T1 (de) | 2005-12-15 |
| US20030166727A1 (en) | 2003-09-04 |
| IL136839A0 (en) | 2001-06-14 |
| EP1289517B1 (fr) | 2005-11-16 |
| JP2004503498A (ja) | 2004-02-05 |
| AU2001274459B2 (en) | 2005-07-07 |
| ES2254432T3 (es) | 2006-06-16 |
| WO2001095899A8 (fr) | 2004-04-29 |
| WO2001095899A2 (fr) | 2001-12-20 |
| CA2411831C (fr) | 2010-07-20 |
| WO2001095899A3 (fr) | 2002-08-08 |
| DE60115029T2 (de) | 2006-08-03 |
| CA2411831A1 (fr) | 2001-12-20 |
| DE60115029D1 (de) | 2005-12-22 |
| AU7445901A (en) | 2001-12-24 |
| EP1289517A2 (fr) | 2003-03-12 |
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